7-(Benzyloxy)naphthalen-2-ol → Binol

Participants

Reaction Steps

A reaction flask described in example 9 was charged with a solution of catalyst 1c (12.2 mg, 0.02 mmol) in anhydrous CCl4 (1 mL). The solution was stirred for 10 min under an oxygen atmosphere and then treated with a solution of 7-benzyloxy-2-naphthol (50 mg, 0.2 mmol) in anhydrous CCl4 (1 mL) under 0° C. The reaction mixture was stirred at 0° C. until the reaction was complete (monitored by TLC). The crude mixture was concentrated under reduced pressure, and purified by column chromatography (Ethyl acetate/Petroleum ether=⅓) to give (R)-BINOL 3g, Yield 80%. [α]D25=−157.4 (c=0.3 in EtOAc), 1HNMR (300 MHz, CDCl3) δ (ppm) 7.89 (d, J=9.0 Hz, 2H, 2×HC (5)), 7.80 (d, J=8.7 Hz, 2H, 2×HC (4)), 7.24 (d, J=9.0 Hz, 2H, 2×HC (3)), 7.10–7.22 (m, 12H, 2×HC (6), 10×PhH), 6.50 (d, J=2.1 Hz, 2H, 2×HC (8)), 5.01 (s, 2H, 2×OH), 4.73.4.84 (m, 4H, 4×OCH2). e.e. 95%.

Provenance & Evidence